Dichloromethane → 2-[(E)-2-(3,5-dimethoxyphenyl)vinyl]-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine

HRID 1052242Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1052242
Br[C:2]1[N:3]=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24](/[CH:30]=[CH:31]/B2OC(C)(C)C(C)(C)O2)[CH:25]=[C:26]([O:28][CH3:29])[CH:27]=1.ClCCl.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[CH3:29][O:28][C:26]1[CH:25]=[C:24](/[CH:30]=[CH:31]/[C:2]2[N:3]=[C:4]3[CH:10]=[CH:9][N:8]([S:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)(=[O:13])=[O:12])[C:5]3=[N:6][CH:7]=2)[CH:23]=[C:22]([O:21][CH3:20])[CH:27]=1

Komponenten

8

Edukt 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 162181852-[(1E)-2-(3,5-Dimethoxyphenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 899634192-Bromo-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine

Produkt 1

HCID 899631882-[(E)-2-(3,5-dimethoxyphenyl)vinyl]-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
88 °C

Versuchsvorschrift

A stirred mixture of 2-bromo-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine (929 mg, 2.75 mmol), 2-[(E)-2-(3,5-dimethoxyphenyl)vinyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (from Aldrich, cat#676160, 838 mg, 2.89 mmol), [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), complex with dichloromethane (1:1) (140 mg, 0.171 mmol), and potassium phosphate (1.20 g, 5.65 mmol) in 1,4-dioxane (20 mL)/water (9.6 mL) was heated at 88° C. After 1 hour, the reaction mixture was quenched with saturated aq. NH4Cl and extracted with methylene chloride. The combined organic layers were dried over MgSO4, filtered, and then concentrated. The residue was purified on silica gel (eluting with 0 to 50% EtOAc in hexanes) to give the desired product (1.10 g, 95%). LCMS calculated for C22H20N3O4S (M+H)+: m/z=422.2. Found: 422.2.

Aufarbeitung

  1. customthe reaction mixture was quenched with saturated aq. NH4Cl
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel (eluting with 0 to 50% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-64b5732f4f374fa8a9f4ed4dcc5735e3
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388185B2

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